Extreme pressure lubricant



Patented June 24, 1941 2,247,042 EXTREME PRESSURE LUBRICANT Henry G. Berger and Darwin E. Badertscher, Woodbury, and Francis M. Seger, Pitman, J assignors to Socony-Vacuum Oil Company, In-

corporated, New York, N.

New York Y., a. corporation of No Drawing. Application'September 25,1940,

Serial No. 358,236

8 Claims.

This invention, which is a continuation in part of that disclosed in our copending application Serial No. 177,891, filed December 3, 1937, relates to lubricant compositions adapted for use as extreme pressure lubricants.

As is well known to those familiar with the art, the ordinary type of hydrocarbon lubricant comprised only of a petroleum fraction is incapable of withstanding the enormous pressures encountered between engaged surfaces in various types of modern machinery such as the hypoid gears used in motor vehicles. This fact has led to the development of the so-called extreme pressure lubricant, which is comprised of a suitable carrying medium such as a viscous mineral oil fraction and a minor proportion of an addition agent which under the extreme pressure conditions encountered will provide or form. between the engaged surfaces a lubricant film capable of withstanding these high pressures.

Ingredients of the type just referred to are known as extreme pressure agents or E. P. bases, and numerous materials have been proposed for such use. Among the various extreme pressure agents which have been proposed and' which have met with varying degrees of success are oil-soluble organic materials which contain sulfur and chlorine. Our present invention is related to this general type of compound;

For the purpose of testing the efiicacy of materials as extreme pressure agents, it is customary to prepare mineral oil blends containing a minor proportion of the agent to be tested and subject the oil blank and the blend to one or more of the various laboratory tests which have been devised to give an indication of the load-carrying capacity of such lubricants. Typical tests recognized in the art as being satisfactory for this purpose are the Almen pin test described by Wolfe and Mougey, Proc. A. P. I. 1932, pages 118-130, and the S. A. E. test described in S. A. E. Journal 39,

The aforesaid copending application Serial No. 177,891 discloses as extreme pressure agents the general class of compounds or reaction products obtained by reacting perchloromethylmercaptan with organic compounds containing replaceable hydrogen orreplaceable metal atoms. The present invention is concerned with a specific group of reaction products falling into that general class, namely, the products obtained by reacting perchloromethylmercaptan with organic amines.

Perchloromethylmercaptan is the chlorinated substituted sulfur chloride having the formula 05014 or ClaC-SC1. It can be prepared by the chlorination of carbon disulfide according to the method of Helfrich, and Reid (Journal American Chemical Society, 43, 591 (1921)). For example, carbon disulfide containing about 0.4 per cent by Weight of iodine was chlorinated in the absence of direct sunlight at a temperature maintained below 25 C. until the volume of the reaction mixture had doubled. The .crude reaction product, which contains carbon tetrachloride and sulfur chloridesin addition to perchloromethylmercaptan, can be used' in the preparation of the reaction products contemplated by this invention, but it is preferable to purify the crude product by distillation on a water bath at about 100 C., followed by steam distillation. Subsequent vacuum-distillation of the material refined in this manner indicated that the steam-distilled material was practically pure.

For the organic amines contemplated herein to obtain reaction products for use as extreme pressure agents, preference is given to the primary and secondary amines. These amines may be aliphatic amines such as monoor diethyl amine, monoor dipropyl amine, monoor dibutyl amine, monoor dicyclohexyl amine, or they may be aromatic amines such as aniline and its derivatives, naphthylamine and its derivatives, etc.

The procedures which may be followed in synthesizing reaction products of the type contemplated herein as extreme pressure agents may be obtained from the following examples describing typical preparations. In these examples we have also given the results of extreme pressure tests showing the effectiveness of these illustrative products in improving the extreme pressure characteristics of a typical mineral oil.

EXAMPLE ONE Reaction products of perchloromethylmercaptan and monobutyl amine or 0.54 equivalent) of sodium carbonate while the perchloromethylmercaptan solution was added thereto. The addition was made at an average temperature of about 10 C., and the rate of addition was such that it consumed about 40 minutes. The petroleum ether solution of the product was Washed and filtered and the solvent removed by placing under a vacuum, of approximately 30 mm.

at room temperature. The final product obtained was a red-brown liquid of low viscosity and a characteristic somewhat sweet odor. The yield was approximately 105 grams. A mineral oil the S. A. E. test at a load of 580+, the machine operating at a speed of 1000 R. P. M. with a 14.6:1 rubbing ratio and a loading rate of 8.35 pounds per second. The 5 per cent mineral oil blend of this product went to a-load of 26,000 pounds in the Almen pin test before failure.

EXAMPLE Two Reaction product of perchloromethylmercaptan and dibutylamine In this preparation 37.2 grams (0.2 mole) of perchloromethylmercaptan and 51.6 grams (0.4 mole) of dibutylamine were reacted together in a benzol solution. The hydrochloride formed was filtered out; the benzol solution of the prod-' EXAMPLE THREE Rea'ctz'on product of perchloromethylmercaptan and dicyclohexylamine In this preparation 51 grams (0.27 mole) of perchloromethylmercaptan and 100 grams (0.55 mole) of dicyclohexylamine' were reacted in ben- 'zol solution. The hydrochloride formed was reblend containing 5 per cent of this product passed moved by filtration and the benzol solution topped on to yield a solid residue. A 5 per cent blend of this product in the same mineral oil the S. A. E. test at a load of 295 pounds. EXAMPLE FOUR Reaction product of perchloromethylmercaptan and ethyl aniline A petroleum ether solution containing 61 grams (0.5 mole) ofhethyl aniline was prepared and mixed with an aqueous solution containing an While stirring this excess of sodium carbonate. solution a petroleum ether solution containing 93 grams (0.5 mole) of perchloromethylmercapdescribed in connection with Example One failed tan was added over a period of about 25 minutes during which the temperature of the reaction mixture was maintained at a temperature of 8 C, The petroleum ether solution containing the reaction product was washed with water, filtered and the solvent removed at room temperature by means of vacuum.

The product obtained after filtering was a light amber liquid of low viscosity and mild odor. The yield was 116 grams. A 5 per cent blend of this product in themineral oil described in connection with Example One failed in the,

S. A. E. test at a load of 290 pounds and the Almen pin test at a load of 26, P u

The blank oil used in the foregoing examples the load-carrying lubricants for use under extreme pressure con-' ditions. It is to be understood that while the foregoing examples describe specific reaction procedures and specific amines for the secondary reactants, the invention is not limited to such,spe-

cific procedural details nor to specific amines but includes within its scope such changes as fairly come within the spirit of the appended claims.

We claim:

1. An extreme pressure lubricant comprising a hydrocarbon lubricating oil and in admixture therewith a minor proportion of the product obtained by the reaction of perchloromethylmercaptan with an organic amine.

2. An extreme pressure lubricant comprising a hydrocarbon lubricating oil and in admixture therewith a minor proportion of the product obtained by the reaction of perchloromethylmercaptan with a primary organic amine.

' 3. An extreme pressure lubricant comprising a hydrocarbon lubricating oil and in admixture therewith a-minor proportion of the product obtained by the reaction of perchloromethylinrcaptan with a secondary organic amine.

4. An extreme pressure lubricant comprising a hydrocarbon lubricating oil and in admixture therewith a minor proportion, from about -0.5

per cent to about 20 percent, of the product obtained by the reaction of perchloromethylmercaptan with an organic amine.

5. An extreme pressure lubricant comprising a hydrocarbon lubricating oil and in admixture therewith a minor proportion. from about 0.5 per cent to about 20 per cent, of the product obtained by the reaction of perchloromethylmercaptan with a primary organic amine;

6. An extreme pressure lubricant comprising a hydrocarbon lubricating oil and in admixture therewith a minor proportion, from about 0.5 per cent to about 20 per cent, of the product obtained by the reaction of perchloromethylmercaptan with a secondary organic amine.

7. An extreme pressure lubricant'comprising a hydrocarbon lubricating oil and in admixture therewith a minor proportion of the product obtained by the reaction of perchloromethylmercaptan with an organic amine, said reaction product being present in an amount suflicient to increase capacity of the oil.

8. An extreme pressure lubricant comprising a hydrocarbon lubricating oiland in admixture therewith a minor proportion, suflicient to increase .the load-carrying capacity of the oil, of

the product obtained by reacting perchloromethylmercaptan with an on'ganic amine selected from the group of monobutyl amine, dibutyl amine, dicyclohexyl amine, and ethyl aniline. HENRY G. BERGER.

DARWIN E. BADERTSCHER. FRANCIS M. SEGER. I 

